Originally Posted by
cloudybw
Originally I booked AAA-MMM-AAA as a simple region 1-region 2 roundtrip. When I called to add AAA-ZZZ at the end, the agent claimed it also errored out on their end. I suspect it would error out once it detects a roundtrip between AAA-MMM. Afterall, ZZZ is in another region other than AAA or MMM, so it is not the same case as in the wiki here.
In theory that should work...as the "free Hawaii leg" ie: USA->Europe->USA->Hawaii for 62.5k miles has been well documented, even though if there is an 'embedded' round-trip.
If it also error's out on their end, the only things I can suggest is asking to be transferred to the rates desk (which should be a bit more knowledgable and may able to manually price it out) or simply trial-and-error with your strategies.